5-(1-pyrrolidinylcarbonyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(1-pyrrolidinylcarbonyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine
• 英文别名: [5-((S)-1-Methyl-pyrrolidin-2-ylmethoxy)-pyridin-3-yl]-pyrrolidin-1-yl-methanone；[5-[[(2S)-1-methylpyrrolidin-2-yl]methoxy]pyridin-3-yl]-pyrrolidin-1-ylmethanone
• 化学式: C₁₆H₂₃N₃O₂
• 分子量: 289.378
• InChiKey: XXVAMDODEUJKKK-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  45.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基-L-脯氨醇 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydride 作用下， 生成 5-(1-pyrrolidinylcarbonyl)-3-(1-methyl-2-(S)-pyrrolidinylmethoxy)pyridine
  参考文献：
  名称：

  Synthesis and structure-activity relationships of pyridine-modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543, a potent nicotinic acetylcholine receptor agonist

  摘要：

  Analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine (A-84543, 1) with 2-, 4-, 5-, and 6-substituents on the pyridine ring were synthesized. These analogs exhibited Ki values ranging from 0.15 to > 9,000 nM when tested in vitro for neuronal nicotinic acetylcholine receptor binding activity. Assessment of functional activity at subtypes of neuronal nicotinic acetylcholine receptors indicates that pyridine substitution can have a profound effect on efficacy at these subtypes, and several subtype-selective agonists and antagonists have been identified. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00019-5

文献信息

• 3-PYRIDYLOXYMETHYL HETEROCYCLIC ETHER COMPOUNDS USEFUL IN CONTROLLING CHEMICAL SYNAPTIC TRANSMISSION
  申请人：Abbott Laboratories

  公开号：EP0934308B1

  公开（公告）日：2004-08-11
• US5629325A
  申请人：——

  公开号：US5629325A

  公开（公告）日：1997-05-13
• US6127386A
  申请人：——

  公开号：US6127386A

  公开（公告）日：2000-10-03
• US6437138B1
  申请人：——

  公开号：US6437138B1

  公开（公告）日：2002-08-20
• Synthesis and structure-activity relationships of pyridine-modified analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine, A-84543, a potent nicotinic acetylcholine receptor agonist
  作者：Nan-Horng Lin、David E Gunn、Yihong Li、Yun He、Hao Bai、Keith B Ryther、Theresa Kuntzweiler、Diana L Donnelly-Roberts、David J Anderson、Jeffrey E Campbell、James P Sullivan、Stephen P Arneric、Mark W Holladay

  DOI：10.1016/s0960-894x(98)00019-5

  日期：1998.2

  Analogs of 3-[2-((S)-pyrrolidinyl)methoxy]pyridine (A-84543, 1) with 2-, 4-, 5-, and 6-substituents on the pyridine ring were synthesized. These analogs exhibited Ki values ranging from 0.15 to > 9,000 nM when tested in vitro for neuronal nicotinic acetylcholine receptor binding activity. Assessment of functional activity at subtypes of neuronal nicotinic acetylcholine receptors indicates that pyridine substitution can have a profound effect on efficacy at these subtypes, and several subtype-selective agonists and antagonists have been identified. (C) 1998 Elsevier Science Ltd. All rights reserved.